


first times a charm

by eddiefuckinkaspbrak



Series: Checkmate [1]
Category: IT (2017), IT - Stephen King
Genre: Alternate Universe - BDSM, Alternate Universe - Modern Setting, Bondage, Bottom Eddie Kaspbrak, Dom/sub, Eddie needs to relax, M/M, Smut, Top Richie Tozier
Language: English
Status: Completed
Published: 2019-06-23
Updated: 2019-06-23
Packaged: 2020-05-18 14:27:52
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 3,836
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19336390
Author URL: https://archiveofourown.org/users/eddiefuckinkaspbrak/pseuds/eddiefuckinkaspbrak
Summary: Eddie Kaspbrak is stressed. Really fucking stressed. Luckily for him his roommate Bill has a solution for him, one that might not only relieve his stress, but change his life.





	first times a charm

**Author's Note:**

> This is the first in a new series called 'checkmate'. Please read the tags for each part in regards to kinks as it's gonna get intense!! Enjoy!

Eddie slammed the door shut to the apartment that he shared with his friend Bill, startling him enough to cause his ramen to spill onto his lap. At first, he didn’t even notice, his mind swimming with stress and his emotions all over the place. It wasn’t until Eddie collapsed onto the chair opposite Bill and looked up, that he saw his friends shocked, and annoyed face.

“You’ve got ramen all-” Eddie started and Bill held up a finger, his eyes narrowing just a little. “What?”

Bill shook his head, cleaning himself up and sitting the bowl of ruined ramen onto the coffee table. “You need to relax,” he muttered after a few moments. “That’s the third time this week you’ve come in pissed and caused me to either spill something or almost break something. One day you’re going to break the front door by slamming it too hard.”

Eddie stopped and his hard posture faded as he sunk back into the sofa, tears welling up in his eyes, “I’m sorry Bill,” he whispered, bringing his knees up to his chest and resting his chin on top of them. “Between work and studying...I just can’t seem to catch a break. I guess all those sleepless nights are catching up on me…”

“Then you need to relax, go out and get laid. When was the last time you had sex anyway?” Bill asked, standing up and walking to the kitchen, placing the bowl in the sink. He turned back around, his eyebrow raised up past his auburn bangs.

“That...is not important,” Eddie mumbled, his cheeks already turning a light shade of red. It wasn’t that he was a prude, or a virgin, because he wasn’t. He just liked to get to know his partners first instead of simply having a one night stand. However...maybe that was where he was going wrong.

Bill crossed back into the living room and sat back down on the couch, a serious look on his face. “I’m serious Eddie, you need to just...let loose. Let someone else take control and just let it happen.” Suddenly a bright smile took over Bill’s face and Eddie didn’t like the way it turned into a smirk. “I know _exactly_ ****what you need. Get dressed into something sexy.”

Eddie spluttered out at Bill’s words and he shook his head, “I’m not...I’m not going out Bill, this is the last thing I want to do.” He started to make his way to his room when Bill grabbed around his wrist. “Let me go Bill.”

“Just trust me okay? Go put on something sexy and believe me, by the end of tonight you won’t be stressed out anymore.” Bill still had that smirk on his face that set Eddie on edge. It was always the same smile he gave when he was about to get them into some situation. Eddie also knew better than to argue with Bill when he was like this, so to avoid arguments he nodded and disappeared down the hall into his room.

His bed was still unmade and curtains drawn after his early leave that morning. He had slept in for his classes and had to rush out without even having a chance to shower. Knowing that Bill probably had something that involved Eddie getting laid in his plans, he slipped into a quick hot shower. As the water ran over his skin, Eddie exhaled, a sense of relaxation coming over him as he washed his hair.

When he was sure he was clean enough, Eddie turned off the hot water and dried off, stepping back into his room and towards his closet. Something sexy, Bill had said and Eddie scoffed, ruffling through his clothes. He wasn’t even sure he _owned_ ****something sexy. He pulled out a pair of short shorts and a sweater that would reach his knees. He slipped them on and looked at himself in his floor length mirror before shoving a pair of his black slip ons. He ran his fingers through his drying curls before rejoining Bill outside

“Well?” Eddie asked, watching his friend look him up and down before he nodded, grabbing his wrist and pulling him towards the door. “Where are we going Bill?” Eddie asked again, hoping his friend would give him some kind of clue as to what he was planning.

Bill didn’t answer, instead he just tugged Eddie out of their dorm and locked the door, leading him down the corridor and out into the busy street of New York. It wasn’t until they had walked about a block that Bill finally spoke up, “We’re going to a club,” he smiled. “But not just any club, this club is...well...you’ll see.”

Something about the way Bill described the place caused something to stir in Eddie’s gut. Was it anticipation? Nerves? Fear of the unknown? He had no idea. He didn’t have to wonder long, as Bill came to a stop outside what looked like a regular club. Regular apart from the neon sign above the doorway that read, **'Checkmate’**.

Before Eddie could even ask what was going on, Bill was tugging him inside, where they were greeted by a tall woman with long red hair and bright red lips. Her eyes seemed to brighten up when she spotted Bill and she approached them, her heels clicking on the floor. “Bill, back again so soon?” She asked and turned her attention to Eddie. “And I see you’ve brought a friend this time.”

“Bev,” Bill greeted, that smirk still on his lips. “Not here for me this time I’m afraid. My roommate, Eddie here is a little stressed out and I think this experience is just what he needs to...relax.”

The woman, Bev, turned her complete attention to Eddie and circled him as though he was some kind of prey. She stopped in front of him again and tilted his head up, her nails lightly scratching over his skin as she did so. “You’re cute,” she grinned, letting go and taking a step back. “You also look confused as fuck. Do you have any idea what we do here?” She asked, giving Bill a pointed look.

“If I told him he definitely wouldn’t have come,” Bill spoke in his defence, raising his hands up, that smirk still in place. “I’ll leave you in Bev’s capable hands,” he winked at Eddie, backing up towards the door. “Enjoy yourself.”

The door opened and closed, leaving Eddie alone with Bev who was still grinning at him, “Oh darling you are in for a treat tonight.”

Eddie, who hadn’t spoken a word since he had walked into the place, finally found his voice. “What is this place?” He asked and Bev wrapped her hand around his wrist, tugging him down a corridor and into a dark room with red coloured walls. She closed the door and gestured for him to take a seat, which he did and she sat down opposite him, pulling out a sheet of paper and sliding it across to him with a pen.

“This is a BDSM club, Eddie,” Bev said seriously. “Now, it’s not like any of the usual clubs in the city, where people just roam around and initiate any old scene with anyone, oh no. This is more...private.” She pointed to the sheet. At this point, Eddie’s cheeks were flushed and he crossed his legs under the table, biting on his lip. “We have twenty rooms here, all private with their own stock. The doms all work for the club and the subs well...the subs are the walk ins. Like you. The sub would fill in this form, ticking what things they liked as well as highlighting things that they do not like.” Bev pointed to the form with a large list of words on it. “Read it carefully and make your choices. I would then match you up with someone and take you to one of the rooms. You would sit on the bed and put on the blindfold and well...wait.”

With a shaky hand, Eddie picked up the pen, uncapping it with his teeth. His stomach swirled and this time he _knew_ ****it was in anticipation. Damn Bill and his ability to read him like an open book. “W-What happens then?” He asked, and as soon as the words were out he felt foolish.

Bev let out a laugh, “Well, the dom would come in and the scene would start. It can last as long as you would like it to last, but ultimately, the dom is in control. You keep the blindfold on the entire time unless you are instructed to remove it.” She smiled and made to stand. “Of course, you don’t have to go any further, you can say that this isn’t for you and leave right now but...I don’t think you want to do that, do you Eddie?”

With a shake of his head, Bev grinned, clapping her hands, “Alrighy, fill in the form and take your time. Ring that little bell there when you’re ready and I’ll come back for you okay?”

Eddie nodded his head and Bev left the room, her heels clicking on the floor as she walked away. When he was sure he was alone, Eddie looked down at the form, swallowing thickly. There was a lot of questions he needed to answer, which was probably for the best, to be on the safe side. This was meant to be pleasurable and if something happened that Eddie didn’t like well...it would defeat the purpose.

With that in mind, he began to fill out the form.

 **Name:** Eddie Kaspbrak  
 **Age:** 23  
 **Experience:** Does porn count?  
 **Prefered Sex:** Male. 100% Male.

As Eddie wrote that down he flushed and bit down on his lip hard. Even though it had always been something he had wanted to try, he had never been able to do it with a physical partner. He knew things that he really wanted to try, things that he was hard set against and things he would be okay with trying. As he said before, he wasn’t a prude or a virgin.

Once all the personal details were done, Eddie turned his attention to the list itself. It was long. Over one hundred things were there and a few he could already give a hard pass to. Once he had crossed out all the definite no’s, he was still left with a lot of kinks which one again, made his cheeks heat up.

_Ageplay, Anal plugs (small, large and public under clothes), Aromas, Blindfolding, Being Bitten, Bondage (All forms), Breathplay, Spanking (with hand, paddle and cane), Chains, Ropeplay, Cuffs (Leather and Metal), Cock rings & Chastity Belts, Edging, Orgasm Denial/ Control, Gags (All forms), Hair Pulling, Degrading/ Dirty talk, Handjobs, Harnessing, Having clothes chosen for you, Lingerie, Blowjobs, Nipple clamps, Punishment scenes, Spreader bars, Teasing, Vibrator on genitals. _

He read over it again and again and again, making sure that he was happy with his options before he rang the bell, just like Beverly had asked him to. A few minutes later, her heels made their approach to the door and she opened it, holding out her hand for the form, which he gave to her without hesitation. She scanned it over quickly and grinned, “You’re very open to a lot of things Eddie...for a first timer.” She winked. “I think I have the _perfect_ ****partner for you sweetcheeks.”

She stepped out of the room once more, vanishing down the hall and Eddie was once again alone. He took that opportunity to look around the room, but there was nothing exciting there, just a few pictures on the wall and a sofa in the corner.

Bev returned less than five minutes later, a wide grin on her face, “Are you ready?” She asked and Eddie nodded his head, standing up to follow her. “This way.” They left the red room and walked further down the corridor. They passed a few doors with numbers on them until they came to a stop outside room number 14. “Here we are,” Bev grinned, unlocking the door and handing Eddie a blindfold. “Your dom asked if you could just sit on the bed fully clothed with the blindfold on. How does that sound?”

Eddie nodded his head, taking the smooth fabric out of her hands and stepping into the room. It was bigger than Eddie expected it to be and his eyes widened. On one side of the room was a large King Sized bed, but there were obviously no sheets and on the other were racks of chains, paddles, toys and...so much more. Everything anyone would need to have a pleasurable experience was in this room.

He didn’t realise Bev was gone until he heard the click of her heels down the corridor and he swallowed, making his way over to the bed. Eddie sat down on the edge, running the blindfold through his fingers before he brought it up to his eyes, tying it around his head as he was engulfed in darkness.

Now all he had to do was wait.

* * * * *

It felt like an hour had passed before Eddie heard the door open and then click shut. His fingers dug into the sheets tight as he strained his ears to hear for any other movement, but he soon realised that his dom must be wearing socks so as to keep him in suspense. His thoughts were right as he felt warm breath behind him at his neck and then a pair of lips move up to his ear.

“My...Bev was right, you are a pretty one,” the man whispered, his voice rough and deep, causing Eddie to gasp out slightly. The man chuckled at his reaction, a hand reaching up around Eddie’s neck and fingers trailing lightly down the skin, “So soft...can’t wait to wreck you.”

Eddie’s lips parted just a little and he brought his thighs together in some attempt to quench the heat that was burning in his stomach. His mind was trying to picture what this man looked like, feeling a little frustrated for the blindfold, but understanding its purpose. This wasn’t about looks, it was about pleasure.

The man coaxed him away from his thoughts as he shifted so he was behind Eddie, his back to the mans firm...and naked chest. With a simple shift of his hand, Eddie felt the man’s legs, which were clad in a pair of jeans. He exhaled as the hands that were on his neck, moved down to his thighs, spreading his legs and hooking them over his knees. “We’ll use the traffic light system. Green is good, yellow is slow down and red is stop. Understood?”

“Yes,” Eddie breathed, nodding his head. Just as the words left his lips, a firm hand came down on his inner thigh and Eddie jumped, his cheeks flushed. “ _Oh!_ **”**

The man chuckled once more, rubbing the skin of his thigh where he had spanked him. “That’s yes _sir_.” He emphasised the sir and Eddie bit his lip. Of course. “Just so you have _some_ ****of an idea though, my name is Richie, but when you’re with me, as my submissive, then you call me sir. Got it?”

“Yes sir,” Eddie gasped out. _Richie_ , his Dom’s name was Richie. Somehow, it was rather fitting.

“Good boy,” Richie breathed into his ear, his large hands massaging his thighs, keeping them wide and spread open. “Now, here’s what’s going to happen tonight. Since this is your first time, I’m going to take it a little easy on you, but not too easy.” His hands moved from Eddie’s thighs to his sweater, pulling it up and dipping a hand past the waistband of his shorts.

Eddie tilted his head back as a whimper of pleasure left his lips. He arched up as Richie’s hand wrapped around his hardening cock, stroking it slow...teasing like. “Th-thank you sir,” he breathed, letting out small pants. He arched up more as Richie’s thumb teased over his slit and he was about to beg for more when he pulled his hand out and moved away.

“Stand up,” Richie ordered and Eddie scrambled to his feet, gripping onto the pole for the bed for balance, his toes curling up in his shoes. “Step forward two steps.” As he did so, Eddie could feel Richie circle him, feel his eyes scanning over his body. “Take off your clothes, all of them.” Not wanting to keep Richie waiting, Eddie pulled off the sweater and then pulled his pants and underwear down before kicking off his shoes and socks.

What followed was a long stretch of silence and Eddie knew that Richie was admiring him as he stood there and waited. Finally, after what felt like a lifetime, Eddie felt a hand on the small of his back, guiding him forward. He let his feet move, wondering where Richie was leading him until they came to a stop and the hand disappeared. “Sir?” He asked quietly, wondering what was happening.

Richie’s hand was back, grounding Eddie for a second. “Arms in the air,” he whispered in Eddie’s ear. “I’m going to cuff them above your head.” Eddie swallowed and did as he was told, raising his hands and he let out a whimper as a leather cuff was strapped around each of his wrists, holding his arms in the air. “God, you are stunning, you have no idea all the things I want to do to you Eddie…” Richie drawled.

“Thank you s- _ir_!” Eddie let out a squeak of surprise as his arms were pulled upwards so he was on his toes, stretched out for Richie. _Holy shit_. He could feel his cock harden even more, which was followed by a dark chuckle from his dom, whose fingers were now wrapped around his ankles.

“Spread your legs,” Richie ordered and Eddie obliged, spreading them as wide as he could and gasping as Richie wrapped cuffs around them too, keeping him in place. “I am a big fan of bondage, if you haven’t already figured that out,” He whispered in Eddie’s ear, his fingers moving up to brush over his lips. “So pretty.”

The fingers moved away from his lips and down his chest, stopping at his nipples. Eddie knew he had very sensitive nipples, and he was already reacting with gasps from Richie just _brushing_ ****over them. “Sir…” he whined, his head falling forward as he pulled on the cuffs.

Just like that the fingers were gone and were replaced by Richie’s teeth and tongue, wrapping around his left nipple and tugging. He bit and scraped and licked over the little nub, before moving onto the right one. Eddie could barely form a coherent word, his mind spinning in pleasure. As Richie continued his assault on his nipples with his mouth, Eddie felt his hand move down between his legs, wrapping around his cock and stroking fast, with purpose. “I want you to come from this, do you hear me? I am going to count down from thirty and if you don’t come, I’ll spank you. Understood?”

“Yes sir,” Eddie panted, rocking his hips forward as much as he could into Richie’s hand. Moans spilled from his lips as Richie picked up the pace of his hand and started to count down from thirty, just like he said he would.

“Thirty…”

“Twenty- five…”

His words were slow, and Eddie could feel his orgasm approaching by the time Richie had reached fifteen. He wondered what would happen if he came _before_ ****Richie got to zero, but he didn’t want to find out.

“Five...four…three...two...one. Come for me Eddie, come on,” Richie breathed into Eddie’s ear and he didn’t need to be told twice. With a cry of pleasure Eddie reached his climax, coming over Richie’s hand in what he could only assume were thick ropes of white come. “Good boy, such a good boy following my instructions. What do you say?

“T-Thank you s-sir!” Eddie gasped out, still coming down from his high. Richie’s hand continued to stroke at his cock until he sagged forward in the restraints, sweat dripping down his forehead.

After a few seconds, Eddie felt Richie uncuff his legs from the restraints and then his wrists, catching him as he fell forward into his arms. He was guided over to the bed and laid down on his stomach, head resting on the pillow. “You were such a good boy for me Eddie,” Riche praised, his hands running up and down his spine, soothing him. “Since this was your first time, we won’t go any further than that...I wanted to give you a tester, to see how you liked it.”

Oh god, did Eddie like it. He was sure he had never come so hard from sex than he did in that short period of Richie stroking him with his hand. “I liked it sir,” he whispered, relaxing into the soft mattress.

“Will you come back?” Richie asked, his hands moving down to cup his ass. “I hope you do before damn, I want to get my hands on that ass.”

That caused a gasp to leave Eddie lips and he felt his toes curl up. If Richie continued the way he was going, Eddie would be hard again. As though sensing that himself, his hands moved back up to his spine. After a second, Eddie nodded his head. “I’ll be back.”

Richie traced his fingers along his spine for a few more minutes before he moved away, running his fingers through Eddie’s curls. “I hope you do, we have barely touched the surface and as I said before...I can’t wait to wreck you.” Eddie felt Richie slip off the bed. “When you hear the door close, you can take off the blindfold okay? There is also a button by the door if you press it when you’re ready, Bev will come back for you.” He whispered into his ear. “Take as much time as you need...and Eddie?”

“Yes sir?” Eddie asked quietly.

“I don’t want you to touch yourself until we see each other again. Understood?”

Oh god. Eddie nodded his head, “Understood sir.”

He could practically sense Richie’s happiness, “Good boy.” That was the last thing Richie said before he left the room. The second the door clicked shut, Eddie pulled the blindfold off and collapsed on his back, staring at the ceiling in both shock and bliss.

“Holy shit.” He breathed and after a few moments, he got off the bed and cleaned himself up changing back into his clothes and ringing the bell.

Beverly was with him within seconds, her eyes curious and he felt his cheeks flush under her gaze. “Well, will you be coming back anytime soon?” She asked when they reached the reception area. Eddie swallowed and he nodded his head.

“Oh I’ll definitely be back.”


End file.
